Methanol Or Ethanol Reactant Patents (Class 568/487)
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Patent number: 10525390Abstract: Disclosed are a powder sintered porous metal with better comprehensive properties, especially with good corrosion resistance to hydrofluoric acid, and a filter element using same. The powder sintered porous metal of the present invention has a porosity of 25-60%, an average pore diameter of 0.5-50 ?m and a weight loss rate of at most 1% after being immersed into a hydrofluoric acid solution with a mass fraction of 5% at room temperature for 20 days; and the powder sintered metal porous body consists of Cu accounting for 23-40 wt %, Si accounting for 0-5% and the balance of Ni, based on the weight of the powder sintered metal porous body. The powder sintered porous metal of the present invention has good mechanical properties and machinability, and excellent corrosion resistance in acid mediums, especially in hydrofluoric acid mediums.Type: GrantFiled: June 30, 2014Date of Patent: January 7, 2020Assignee: Intermet Technologies Chengdu Co., Ltd.Inventors: Lin Gao, Tao Wang, Bo Li
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Patent number: 9834501Abstract: A process is described that uses a silver catalyst to convert methanol into formaldehyde in the presence of less than a stoichiometric amount of oxygen. The resulting formaldehyde is reacted without isolation with propionaldehyde over a commercially available anatase titania catalyst that is shown to be catalytically active towards the formation of methacrolein from formaldehyde and propionaldehyde with conversions and selectivities close to 90%. This titania catalyst is readily available, non-toxic, and can be used with formaldehyde and a variety of other aldehyde compounds to make ?,?-unsaturated aldehyde compounds. This process benefits from low raw material costs and is economically advantaged due to the elimination of catalyst separation. This process shows promising stability and selectivity during lifetime studies, particularly when performed in the presence of a hydrogen carrier gas.Type: GrantFiled: January 28, 2016Date of Patent: December 5, 2017Assignee: Eastman Chemical CompanyInventors: Venkata Bharat Boppana, David William Norman, Gerald C. Tustin, Melissa Page Steffey
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Patent number: 9828322Abstract: A commercially available anatase titania catalyst is shown to be catalytically active towards the formation of methacrolein from formaldehyde and propionaldehyde with conversions and selectivities close to 90%. This titania catalyst is readily available, non-toxic, and can be used with formaldehyde and a variety of other aldehyde compounds to make ?,?-unsaturated aldehyde compounds. This process benefits from low raw material costs and is economically advantaged due to the elimination of catalyst separation. An additional advantage of this method involves the ability of the catalyst to be fully regenerated after a calcination step at 450° C. in air. This process shows promising stability and selectivity during lifetime studies, particularly when performed in the presence of a hydrogen carrier gas.Type: GrantFiled: January 28, 2016Date of Patent: November 28, 2017Assignee: Eastman Chemical CompanyInventors: Venkata Bharat Boppana, David William Norman, Gerald C. Tustin, Melissa Page Steffey
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Patent number: 9731261Abstract: In a process for carrying out a chemical reaction gaseous reactants are supplied to a first reaction zone including a first catalyst having a first particle equivalent diameter. The first reaction zone is operated such that when the reactants are contacted with the first catalyst a portion of the reactants is converted to the desired product. An intermediate stream of unreacted reactants and the desired product is removed and passed to a second reaction zone including a tubular reactor. Tubes of the reactor are catalyst carriers containing a second catalyst having a second particle equivalent diameter smaller than the first particle equivalent diameter. The second reaction zone is operated such that when the unreacted reactants are contacted with the second catalyst, at least some of the unreacted reactants are converted to the desired product. A product stream is then recovered. Apparatus for carrying out the process is also described.Type: GrantFiled: January 15, 2015Date of Patent: August 15, 2017Assignee: Johnson Matthey Davy Technologies LimitedInventors: Duncan David Holdsworth, Julian Stuart Gray
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Patent number: 9718754Abstract: Disclosed is a process for the reductive carbonylation of a low molecular weight alcohol to produce the homologous aldehyde and/or alcohol. The process includes conducting the reaction to produce the aldehyde in the presence of a single component catalyst complex composed of cobalt, an onium cation and iodide in a ratio of 1:2:4 without additional promoters. A ruthenium co-catalyst is used in the production of the homologous alcohol. The reductive carbonylation reaction does not require an additional iodide promoter and produces a crude reductive carbonylation product substantially free of methyl iodide.Type: GrantFiled: May 13, 2016Date of Patent: August 1, 2017Assignee: Eastman Chemical CompanyInventors: Jonathan Michael Penney, David William Norman, Andrew James Vetter
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Patent number: 9365479Abstract: Disclosed is a process for the reductive carbonylation of a low molecular weight alcohol to produce the homologous aldehyde and/or alcohol. The process includes conducting the reaction to produce the aldehyde in the presence of a single component catalyst complex composed of cobalt, an onium cation and iodide in a ratio of 1:2:4 without additional promoters. A ruthenium co-catalyst is used in the production of the homologous alcohol. The reductive carbonylation reaction does not require an additional iodide promoter and produces a crude reductive carbonylation product substantially free of methyl iodide.Type: GrantFiled: December 30, 2014Date of Patent: June 14, 2016Assignee: Eastman Chemical CompanyInventors: Jonathan Michael Penney, David William Norman, Andrew James Vetter
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Patent number: 8865943Abstract: The invention provides a process for preparing higher alcohols and/or aldehydes and also mixtures thereof by catalytic reaction of ethanol, the reaction taking place in the presence of at least one catalyst, the catalyst comprising an activated-carbon substrate which is provided with at least one metal, and more particularly has at least one metal dope.Type: GrantFiled: May 5, 2011Date of Patent: October 21, 2014Assignee: Fraunhofer-Gesellschaft zur Forderung der Angewandten ForschungInventors: Andreas Menne, Axel Kraft
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Patent number: 8865614Abstract: A process for producing a ringlike oxidic shaped body by mechanically compacting a pulverulent aggregate introduced into the fill chamber of a die, wherein the outer face of the resulting compact corresponds to that of a frustocone.Type: GrantFiled: February 28, 2013Date of Patent: October 21, 2014Assignee: BASF SEInventors: Knut Eger, Jens Uwe Faust, Holger Borchert, Ralf Streibert, Klaus Joachim Mueller-Engel, Andreas Raichle
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Publication number: 20140094617Abstract: A chemical reactor including: a plurality of heat exchange plates which between them define reaction compartments, in which reactor each heat exchange plate includes two walls between them defining at least one heat exchange space, the respective walls being fixed together by joining regions, and the reactor also comprises at least one injection device for injecting substance into the reaction compartments, said substance-injection device passing through the heat-exchange plates in respective joining regions thereof. Also, a chemical reaction process that can be carried out in this reactor.Type: ApplicationFiled: June 1, 2012Publication date: April 3, 2014Applicant: ARKEMA FRANCEInventor: Jean-Luc Dubois
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Publication number: 20130211146Abstract: The invention provides a process for preparing higher alcohols and/or aldehydes and also mixtures thereof by catalytic reaction of ethanol, the reaction taking place in the presence of at least one catalyst, the catalyst comprising an activated-carbon substrate which is provided with at least one metal, and more particularly has at least one metal dope.Type: ApplicationFiled: May 5, 2011Publication date: August 15, 2013Inventors: Andreas Menne, Axel Kraft
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Patent number: 8471070Abstract: The method for catalytic conversion of alcohols according to the present invention using a zinc oxide catalyst comprises a thermal pretreatment stage in an inert and/or reducing atmosphere at a temperature of at least 100° C., prior to the reaction stage.Type: GrantFiled: May 6, 2011Date of Patent: June 25, 2013Assignees: IFP Energies nouvelles, Centre National de la Recherche Scientifique, Universite de Paris 6—Pierre et Marie Curie Laboratoire Reactivite de SurfaceInventors: Charlotte Drouilly, Guylene Costentin, Helene Lauron-Pernot, Delphine Bazer-Bachi, Celine Chizallet, Vincent Lecocq
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Publication number: 20110288342Abstract: The method for catalytic conversion of alcohols according to the present invention using a zinc oxide catalyst comprises a thermal pretreatment stage in an inert and/or reducing atmosphere at a temperature of at least 100° C., prior to the reaction stage.Type: ApplicationFiled: May 6, 2011Publication date: November 24, 2011Applicants: IFP ENERGIES NOUVELLES, UNIVERSITE DE PARIS 6 - PIERRE ET MARIE CURIE, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUEInventors: Charlotte DROUILLY, Guylene Costentin, Helene Lauron-Pernot, Delphine Bazer-Bachi, Celine Chizallet, Vincent Lecocq
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Patent number: 8062482Abstract: A method for removing acetaldehyde from a mixture of methyl acetate, methanol and acetaldehyde includes: (a) feeding the mixture of methyl acetate, methanol and acetaldehyde to a distillation column; (b) distilling the feed mixture of methyl acetate methanol and acetaldehyde at a pressure of 10 psig or more to generate an overhead vapor stream enriched in acetaldehyde as compared with the feed mixture and a residue stream depleted in acetaldehyde as compared with the feed mixture; and (c) withdrawing the residue stream depleted in acetaldehyde from the distillation column.Type: GrantFiled: October 30, 2007Date of Patent: November 22, 2011Assignee: Celanese International CorporationInventor: R. Jay Warner
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Patent number: 7847129Abstract: A method for dehydrogenating primary or secondary alcohols having 1 to 12 carbon atoms to give the corresponding aldehydes or ketones in which the alcohol is brought into contact with a catalytically active composition comprising an active component of the formula PdaBibYcZd, where Y is selected from the group consisting of Co, Rh, Pt, Ag, Au, and Z is selected from the group consisting of Na, Cs, Mg, Ca, Ba, V, Cr, W, Fe, Ni, Cu, Sb where the indices a, b, c and d give the mass ratios of the respective elements to one another, where a=0.1-3, b=0.1-3, c=0-3, d=0-1.Type: GrantFiled: July 9, 2007Date of Patent: December 7, 2010Assignee: BASF AktiengesellschaftInventors: Heiko Urtel, Soo Yin Chin, Thorsten Johann
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Patent number: 7745667Abstract: Methods for controlling series or series-parallel reactions are described. Novel microchannel apparatus having mesoporous structures adjacent to bulk flow paths are described. Methods of synthesizing formaldehyde from methanol are also described.Type: GrantFiled: April 7, 2008Date of Patent: June 29, 2010Assignee: VelocysInventors: Soumitra Deshmukh, Anna Lee Tonkovich, Terry Manzanec, Bin Yang, Kai Jarosch, Richard Long, Francis P. Daly
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Publication number: 20100016640Abstract: The invention relates to a coated catalyst, especially for oxidation of methanol to formaldehyde, which, on an inert, preferably essentially nonporous, support body, has at least one coating which comprises, before the removal of the organic fractions of components b) and c): (a) oxides, or precursor compounds convertible to the corresponding oxides, of molybdenum and iron, where the molar ratio of Mo:Fe is between 1:1 and 5:1, and optionally further metallic components or metal oxide components or precursor compounds convertible to the corresponding oxides, (b) at least one organic binder, preferably an aqueous dispersion of copolymers, especially selected from vinyl acetate/vinyl laurate, vinyl acetate/ethylene, vinyl acetate/acrylate, vinyl acetate/maleate, styrene/acrylate or mixtures thereof, and (c) at least one further component selected from the group consisting of SiO2 sol or precursors thereof, Al2O3 sol or precursors thereof, ZrO2 sol or precursors thereof, TiO2 sol or precursors thereof, waterglasType: ApplicationFiled: November 23, 2006Publication date: January 21, 2010Applicant: SUD-CHEMIE AGInventors: Christian Guckel, Klaus Wanninger, Marvin Estenfelder, Claudia Fischer, Uwe Durr
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Publication number: 20100010238Abstract: A process for producing a ringlike oxidic shaped body by mechanically compacting a pulverulent aggregate introduced into the fill chamber of a die, wherein the outer face of the resulting compact corresponds to that of a frustocone.Type: ApplicationFiled: June 30, 2009Publication date: January 14, 2010Applicant: BASF SEInventors: Knut Eger, Jens Uwe Faust, Holger Borchert, Ralf Streibert, Klaus Joachim Muller-Engel, Andreas Raichle
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Publication number: 20090326279Abstract: The disclosed technology relates to an apparatus, comprising: at least one microchannel, the microchannel comprising at least one heat transfer wall; a porous thermally conductive support in the microchannel in contact with the heat transfer wall; a catalyst or a sorption medium supported by the porous support; and a heat source and/or heat sink in thermal contact with the heat transfer wall.Type: ApplicationFiled: May 25, 2006Publication date: December 31, 2009Inventors: Anna Lee Tonkovich, Kai Tod Paul Jarosch, Jeffrey D. Marco, Bin Yang, Sean Patrick Fitzgerald, Steven T. Perry, Thomas Yuschak, Francis P. Daly, Haibiao Chen
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Publication number: 20090312581Abstract: A method for dehydrogenating primary or secondary alcohols having 1 to 12 carbon atoms to give the corresponding aldehydes or ketones in which the alcohol is brought into contact with a catalytically active composition comprising an active component of the formula PdaBibYcZd, where Y is selected from the group consisting of Co, Rh, Pt, Ag, Au, and Z is selected from the group consisting of Na, Cs, Mg, Ca, Ba, V, Cr, W, Fe, Ni, Cu, Sb where the indices a, b, c and d give the mass ratios of the respective elements to one another, where a=0.1-3, b=0.1-3, c=0-3, d=0-1.Type: ApplicationFiled: July 9, 2007Publication date: December 17, 2009Applicant: BASF SEInventors: Heiko Urtel, Soo Yin Chin, Thorsten Johann
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Patent number: 7381851Abstract: A process for preparing formaldehyde by gas-phase oxidation of methanol vapor by means of a gas stream comprising molecular oxygen in the presence of a fixed-bed catalyst comprising iron and molybdenum, wherein the process is carried out in a reactor (1) having heat-exchange plates (2) which are arranged in the longitudinal direction of the reactor (1) and have a spacing between them and through which a heat transfer medium flows, inlet and outlet facilities (3, 4) for the heat transfer medium to the heat-exchange plates (2) and also gaps (5) between heat-exchange plates (2) in which the fixed-bed catalyst is present and into which the methanol vapor and the gas stream comprising molecular oxygen are passed, is described.Type: GrantFiled: December 23, 2004Date of Patent: June 3, 2008Assignee: BASF AktiengesellschaftInventors: Gerhard Olbert, Thorsten Johann, Markus Weber, Neven Lang, Eckhard Ströfer, Martin Fiene, Markus Siegert
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Patent number: 6909019Abstract: A process is disclosed for preparing aldehydes by isomerization of the corresponding unsaturated primary alcohols using a transition metal catalyst system, in an alcoholic solvent and in the presence of an acid. An aldehyde forms by isomerizing an unsaturated primary alcohol under conditions that protect the newly formed aldehyde as a dialkylacetal in situ during the reaction. Protecting the aldehyde as an acetal allows for facile separation of the product from the catalyst as well as effectively driving the reaction toward completion.Type: GrantFiled: May 25, 2004Date of Patent: June 21, 2005Assignee: Eastman Chemical CompanyInventor: Sheryl Davis Debenham
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Publication number: 20030176744Abstract: A process and apparatus for oxidizing methanol in a gas stream into formaldehyde in a fixed bed reactor. The process first introduces a gas stream into a fixed bed reactor. The fixed bed reactor contains a catalyst bed having a depth, a width, a length, an inlet, an upstream region, a downstream region and an outlet. Preferably, the inlet, the upstream region, the downstream region and the outlet are provided in the order stated. A vanadia-titania catalyst is provided in the upstream region and a molybdena-titania catalyst is provided in the downstream region. The vanadia-titania catalyst in the upstream region is substantially free of MoO3 and initially (i.e., during oxidation some V2O5 may sublime and migrate to the downstream region) the molybdena-titania catalyst in the downstream region is substantially free of V2O5. Next, the gas stream is contacted with the vanadia-titania catalyst under oxidizing conditions.Type: ApplicationFiled: March 14, 2003Publication date: September 18, 2003Applicant: Lehigh UniversityInventor: Israel E. Wachs
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Publication number: 20030171624Abstract: A process and a catalyst reaction zone comprising one or more fixed bed reactors for oxidizing methanol in a reactant gas feed stream to formaldehyde. According to one embodiment, the process comprises introducing the reactant gas feed stream into an upstream region containing a vanadia-titania first catalyst (substantially free of a volatile MoO3 species) under oxidizing conditions to form a partially oxidized reactant gas feed stream which is then introduced under oxidizing conditions into a downstream region containing a metal molybdate second catalyst to further oxidize any residual methanol contained therein. According to another embodiment, a fixed bed reactor comprising an upstream region and a downstream region containing the aforementioned vanadia-titania and metal molybdate catalysts, respectively, is utilized to implement the inventive process to yield a product gas stream containing formaldehyde preferably at a conversion of 85% or more and a selectivity of 90% or more.Type: ApplicationFiled: March 12, 2003Publication date: September 11, 2003Applicant: Georgia-Pacific Resins, Inc.Inventors: Israel E. Wachs, Ray P. Bourne
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Patent number: 6479710Abstract: A solid acid-base catalyst contains vanadium pentoxide hydrate. Moreover, it is preferable that the vanadium pentoxide hydrate in the solid acid-base catalyst has a composition which is represented by the following general equation (1): V2O5.nH2O (1) (n: 0.1-3). Creation of the vanadium pentoxide hydrate was confirmed by measuring X-ray diffraction spectrum shown in FIG. 1. In accordance with the above arrangement, the solid acid-base catalyst can sufficiently display catalytic activity under mild conditions, and it can be suitably applied to various reactions, such as the syntheses of olefins or ethers through dehydration reactions of alcohols, the syntheses of aldehydes or ketones through dehydrogenation reactions of alcohols, hydrations and isomerization reactions of olefins, alkylations, esterifications, amidations, acetalizations, aminations, hydrogen shift reactions, aldol condensation reactions and polymerization reactions.Type: GrantFiled: March 15, 1999Date of Patent: November 12, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Nobuji Kishimoto, Etsushige Matsunami
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Patent number: 6472566Abstract: An apparatus for preparing formaldehyde from methanol by dehydrogenation in a reactor in the presence of a catalyst at a temperature in the range from 300 to 1000° C., a carrier gas stream which has a temperature above the dehydrogenation temperature is fed to the reactor.Type: GrantFiled: March 1, 2002Date of Patent: October 29, 2002Assignee: Ticona GmbHInventors: Elke Schweers, Thomas Kaiser, Michael Haubs, Michael Rosenberg
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Publication number: 20020062048Abstract: A process and fixed bed reactor for oxidizing methanol in a reactant gas feed stream to formaldehyde. The process comprises introducing the reactant gas feed stream into an upstream region containing a first metal molybdate catalyst (substantially free of a volatile Mo/MoO3 species) under oxidizing conditions to form a partially oxidized reactant gas feed stream which is then introduced under oxidizing conditions into a downstream region containing a second metal molybdate catalyst to further oxidize any residual methanol contained therein. A fixed bed reactor comprising an upstream region and a downstream region containing the aforementioned first and second metal molybdate catalysts, respectively, is utilized to implement the inventive process to yield a product gas stream containing formaldehyde preferably at a conversion of 85% or more and a selectivity of 90% or more.Type: ApplicationFiled: September 13, 2001Publication date: May 23, 2002Inventors: Israel E. Wachs, Laura Briand
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Patent number: 6388102Abstract: Processes for making trioxane, polyoxymethylene and polyoxymethylene copolymers from formaldehyde, made by the dehydrogenation of methanol in the presence of a catalytic active species set free from a sodium compound, at a temperature in the range of 300° C. to 1000° C., wherein a carrier gas stream which has a temperature above the dehydrogenation temperature is fed to the reactor.Type: GrantFiled: July 9, 2001Date of Patent: May 14, 2002Assignee: Ticona GmbHInventors: Elke Schweers, Thomas Kaiser, Michael Haubs, Michael Rosenberg
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Publication number: 20020055658Abstract: A process and apparatus for oxidizing methanol in a gas stream into formaldehyde in a fixed bed reactor. The process first introduces a gas stream into a fixed bed reactor. The fixed bed reactor contains a catalyst bed having a depth, a width, a length, an inlet, an upstream region, a downstream region and an outlet. Preferably, the inlet, the upstream region, the downstream region and the outlet are provided in the order stated. A vanadia-titania catalyst is provided in the upstream region and a molybdena-titania catalyst is provided in the downstream region. The vanadia-titania catalyst in the upstream region is substantially free of MoO3 and initially (i.e., during oxidation some V2O5 may sublime and migrate to the downstream region) the molybdena-titania catalyst in the downstream region is substantially free of V2O5. Next, the gas stream is contacted with the vanadia-titania catalyst under oxidizing conditions.Type: ApplicationFiled: September 13, 2001Publication date: May 9, 2002Inventor: Israel E. Wachs
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Publication number: 20020055659Abstract: A process and a catalyst reaction zone comprising one or more fixed bed reactors for oxidizing methanol in a reactant gas feed stream to formaldehyde. According to one embodiment, the process comprises introducing the reactant gas feed stream into an upstream region containing a vanadia-titania first catalyst (substantially free of a volatile MoO3 species) under oxidizing conditions to form a partially oxidized reactant gas feed stream which is then introduced under oxidizing conditions into a downstream region containing a metal molybdate second catalyst to further oxidize any residual methanol contained therein. According to another embodiment, a fixed bed reactor comprising an upstream region and a downstream region containing the aforementioned vanadia-titania and metal molybdate catalysts, respectively, is utilized to implement the inventive process to yield a product gas stream containing formaldehyde preferably at a conversion of 85% or more and a selectivity of 90% or more.Type: ApplicationFiled: September 13, 2001Publication date: May 9, 2002Inventors: Israel E. Wachs, Ray P. Bourne
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Patent number: 6350918Abstract: Preparing an aldehyde from an alcohol by contacting the alcohol in the presence of oxygen with a catalyst prepared by contacting an intimate mixture containing metal oxide support particles and particles of a catalytically active metal oxide from Groups VA, VIA, or VIIA, with a gaseous stream containing an alcohol to cause metal oxide from the discrete catalytically active metal oxide particles to migrate to the metal oxide support particles and to form a monolayer of catalytically active metal oxide on said metal oxide support particles.Type: GrantFiled: April 17, 2001Date of Patent: February 26, 2002Assignee: Lehigh UniversityInventors: Israel E. Wachs, Yeping Cai
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Patent number: 6339175Abstract: In a process for preparing formaldehyde from methanol by dehydrogenation in a reactor in the presence of a catalyst at a temperature in the range from 300 to 1000° C., a carrier gas stream which has a temperature above the dehydrogenation temperature is fed to the reactor.Type: GrantFiled: February 22, 2000Date of Patent: January 15, 2002Assignee: Ticona GmbHInventors: Elke Schweers, Thomas Kaiser, Michael Haubs, Michael Rosenberg
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Patent number: 6329555Abstract: Described is a process for preparing substituted butenes of the formula I and/or II, where the radical R is unsubstituted or mono- or di-C1-C10-alkoxy-substituted or mono- or dihydroxy-substituted C2-C20-alkyl or alkenyl or is C6-C10-aryl, C7-C11-aralkyl or methyl by reacting 1,3-butadiene with an alcohol of the formula ROH in which R is as defined in the presence of an acidic particulate catalyst insoluble in the reaction medium, which involves contacting the butadiene, the alcohol and the catalyst in a fluidized bed reactor which is flow-approached from below and is operated at above the loosening point.Type: GrantFiled: November 2, 1999Date of Patent: December 11, 2001Assignee: BASF AktiengesellschaftInventors: Maik Aron, Ralf Böhling, Peter Zehner
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Patent number: 6166265Abstract: Process for the preparation of n-butyraldehyde and/or n-butanol, whereina) 1,3-Butadiene or a butadiene-containing hydrocarbon mixture is reacted with an alcohol of the formula IROH I,where R is C.sub.2 -C.sub.20 -alkyl or alkenyl which is unsubstituted or substituted by 1 or 2 C.sub.1 -C.sub.10 -alkoxy or hydroxyl groups, or is C.sub.6 -C.sub.10 -aryl, C.sub.7 -C.sub.Type: GrantFiled: September 15, 1999Date of Patent: December 26, 2000Assignee: BASF AktiengesellschaftInventors: Jurgen Kanand, Rocco Paciello, Michael Roper
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Patent number: 6111139Abstract: A compound having the formula 3,3,3-trifluoropropanal oxime, and an improved process for forming 3,3,3-trifluoropropanal and its oxime. The process for producing 3,3,3-trifluoropropanal involves reacting an alkali or alkaline earth metal salt of an alcohol, which alcohol has the formula ROH, where R is a C.sub.1 -C.sub.4 alkyl, with CF.sub.3 CH.dbd.CHCl under conditions sufficient to yield a product mixture comprising at least one of CH.sub.3 CH.dbd.CHOR and CF.sub.3 CH.sub.2 CH(OR).sub.2 ; and then reacting the product mixture of with a C.sub.3 -C.sub.16 alkanoic acid, and heating under conditions sufficient to form 3,3,3-trifluoropropanal. The oxime is prepared by reacting hydroxylamine with 3,3,3-trifluoropropanal under conditions sufficient to produce 3,3,3-trifluoropropanal oxime.Type: GrantFiled: November 4, 1999Date of Patent: August 29, 2000Inventor: Michael Van Der Puy
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Patent number: 5986146Abstract: A process for the heterogeneous exothermic synthesis of formaldehyde, in particular in a reactor of the type comprising a plurality of adiabatic catalytic beds connected in series, provides the step of feeding to the reactor the methanol necessary for the synthesis distributed in at least two portions, each fed to respective distinct catalytic beds.Type: GrantFiled: December 5, 1997Date of Patent: November 16, 1999Assignee: Floriall Holdings LimitedInventor: Giancarlo Sioli
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Patent number: 5959154Abstract: A process for the heterogeneous exothermic synthesis of formaldehyde, in particular in reactors of the type comprising a plurality of adiabatic catalytic beds connected in series, provides the step of flowing the gaseous reagents across at least one of the catalytic beds with substantially radial flow.Type: GrantFiled: December 1, 1997Date of Patent: September 28, 1999Assignee: Floriall Holdings LimitedInventor: Giancarlo Sioli
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Patent number: 5786518Abstract: A novel process for the manufacture of a .gamma.-halotiglic aldehyde HalH.sub.2 C--CH.dbd.C(CH.sub.3)--CHO ?I!, wherein Hal signifies chlorine or bromine, comprises haloalkoxylating a 1-alkoxy-2-methyl-1,3-butadiene H.sub.2 C.dbd.CH--C(CH.sub.3).dbd.CH--OR.sup.1 ?II!, wherein R.sup.1 signifies C.sub.1-4 -alkyl, using a particular halogenating agent in a C.sub.1-4 -alkanol (R.sup.2 OH) and hydrolyzing the thus-obtained .gamma.-halotiglic aldehyde dialkyl acetal HalH.sub.2 C--CH.dbd.C(CH.sub.3)--CH(OR.sup.1)(OR.sup.2) ?III! to the desired .gamma.-chloro- or .gamma.-bromotiglic aldehyde I. The halogenating agent used in this process is selected from an alkali metal hypochlorite, an alkali metal hypobromite, an alkaline earth metal hypochlorite, an alkaline earth metal hypobromite, tert.butyl hypochlorite, N-bromoacetamide, 1.3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin. Further aspects of the present invention are the use of the thus-manufactured .gamma.Type: GrantFiled: August 1, 1997Date of Patent: July 28, 1998Assignee: Roche Vitamins Inc.Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
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Patent number: 5705707Abstract: A process for the preparation of n-butyraldehyde and/or n-butanol, whereina) 1,3-butadiene is caused to react with an alcohol of the formula IROH I,to form a mixture of adducts of the formulas II ##STR1## and III ##STR2## b) the adduct III is isomerized to the adduct II, c) the adduct II is isomerized in the presence of a homogeneous or heterogeneous transition metal element catalyst to form the enol ether of the formula IV ##STR3## and d) n-butyraldehyde and/or n-butanol is/are produced from this ether IV by the reaction thereof with hydrogen and water or water only in the presence of a homogeneous or heterogeneous catalyst.Type: GrantFiled: July 12, 1996Date of Patent: January 6, 1998Assignee: BASF AktiengesellschaftInventors: Jurgen Kanand, Michael Roper, Rolf Pinkos, Rocco Paciello, Alfred Thome
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Patent number: 5559275Abstract: A process is provided for the production of branched C.sub.4+ oxygenates from lower alcohols such as methanol, ethanol, propanol and mixtures thereof. The process comprises contacting the lower alcohols with a solid catalyst comprising a mixed metal oxide support having components selected from the group consisting of oxides of zinc, magnesium, zirconia, titanium, manganese, chromium, and lanthanides, and an activation metal selected from the group consisting of Group VIII metal, Group IB metals, and mixtures thereof. The advantage of the process is improved yields and selectivity to isobutanol which can subsequently be employed in the production of high octane motor gasoline.Type: GrantFiled: February 21, 1995Date of Patent: September 24, 1996Assignee: UOPInventor: Paul T. Barger
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Patent number: 5554790Abstract: In a process for producing acetic anhydride and acetic acid by reacting methanol and methyl acetate, optionally together with dimethyl ether, with carbon monoxide, acetic anhydride and acetic acid are effectively produced with the use of a sequence of production facilities by carrying out separation of low-boiling point fraction mainly consisting of methyl iodide, methyl acetate and dimethyl ether with the use of at least two distillation zones, separating catalyst drops entrained from the vapor-liquid separation zone in at least one distillation zone and further by controlling the pressurization of the vapor-liquid separation zone and the above distillation zones under 5 bar to a pressure greater than atmospheric pressure.Type: GrantFiled: March 22, 1995Date of Patent: September 10, 1996Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshiyuki Harano, Yoshiaki Morimoto
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Patent number: 5401884Abstract: Formaldehyde is prepared by oxidative dehydrogenation of methanol in the gas phase on a silver or silver-containing catalyst by means of an oxygen-containing gas which contains dinitrogen oxide.Type: GrantFiled: May 6, 1994Date of Patent: March 28, 1995Assignee: BASF AktiengesellschaftInventors: Rainer Diercks, Manfred Essig, Laszlo Marosi
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Patent number: 5330958Abstract: A configuration of cylindrical catalyst granules displays a trilobed or triangular cross-section provided with three through-bores equidistant from each other, each of which through-bores has its axis parallel to the axis of the cylindrical granule.Type: GrantFiled: December 1, 1992Date of Patent: July 19, 1994Assignee: Montecatini Technologie S.p.A.Inventors: Augusto Viola, Massimo Brusa, Bernardo Merighi, Giuseppe Gubitosa
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Patent number: 5132465Abstract: Primary alcohols may be oxidized to the corresponding aldehydes using non-toxic oxidizing agents such as tert-butyl hydroperoxide (TBHP) in the presence of a transition metal phthalocyanine catalyst. Representative catalysts include ferrous phthalocyanine and chloroferric phthalocyanine. Under some conditions, 1,1-dialkoxyalkanes may be co-produced with the aldehydes. 1,1-Dialkoxyalkanes are protected aldehydes and find utility in solvents.Type: GrantFiled: April 23, 1991Date of Patent: July 21, 1992Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
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Patent number: 5008463Abstract: The process dehydrogenates methanol in the presence of a catalyst based on aluminum oxide, alkali metal aluminate and/or alkaline earth metal aluminate with the exclusion of oxygen at a temperature of 650.degree. to 1050.degree. C. in a reactor whose inner wall is composed entirely or partly of aluminum oxide. The process gives anhydrous formaldehyde which contains only very minor impurities.Type: GrantFiled: June 21, 1990Date of Patent: April 16, 1991Assignee: Hoechst AktiengesellschaftInventors: Horst-Philipp Beck, Gerhard Emig, Gunther Wiesgickl, Karlheinz Burg, Karl-Friedrich Muck
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Patent number: 4990685Abstract: In a process for the preparation of aqueous formaldehyde solutions consisting of the following steps:(a) reaction of a methanol/water/air mixture in vapor form at elevated temperature over a catalyst,(b) absorption of the reaction mixture in one or more successive absorption stages with the formation of a methanol-containing aqueous formaldehyde solution and(c) removal by fractional distillation of a fraction esentially containing methanol and water,the methanol/water/air mixture which is required for the reaction is evaporated by means of heat which is withdrawn by indirect heat exchange from the formaldehyde solution being formed in the absorber and/or at least some of the vapors obtained by fractional distillation are condensed by means of liquid water. This condensate is fed together with fresh methanol and with air into the evaporator which is upstream from the catalyst stage.Type: GrantFiled: June 27, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Heinz-Jurgen Alpers, Karl-Heinz Dietz, Bernd-Ulrich Schenke, Reinhard Thiel
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Patent number: 4939292Abstract: Esters are prepared by contacting, under suitable reaction conditions, a feed stream comprising a primary alcohol of 1-4 carbon atoms per molecule (preferably methanol, ethanol) and carbon monoxide with a catalyst composition comprising (a) copper or a copper compound (preferably CuO), (b) zinc oxide, (c) at least one metal or compound of at least one metal selected from the group consisting of cobalt, ruthenium, iridium, platinum, molybdenum, and rhenium (preferably cobalt and/or rhenium) and, optionally, (d) alumina.Type: GrantFiled: October 2, 1985Date of Patent: July 3, 1990Assignee: Phillips Petroleum CompanyInventors: David J. Elliott, Filippo Pennella
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Patent number: 4908477Abstract: Organic iodine compounds are separated from carbonylation products of methanol, methyl acetate and dimethyl ether and from mixtures of such carbonylation products by a process wherein the iodine compounds are removed by liquid phase extraction with a non-aromatic hydrocarbon.Type: GrantFiled: March 9, 1987Date of Patent: March 13, 1990Assignee: BASF AktiengesellschaftInventors: Horst Hartmann, Waldhelm Hochstein, Gerd Kaibel, Franz-Josef Mueller
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Patent number: 4788347Abstract: Formaldehyde is prepared by dehydrogenating methanol in the substantial absence of oxygen and in the presence of a catalyst which is a zinc-silicon complex oxide obtained by mixing a solution containing a zinc salt of an inorganic or organic acid with a solution containing an inorganic silicate compound, or by adding urea to a solution containing a zinc salt of an inorganic or organic acid and an organic silicate compound, until a precipitate is formed, and subsequently baking the precipitate at at least 500.degree. C.Type: GrantFiled: September 18, 1987Date of Patent: November 29, 1988Assignee: Sumitomo Chemical Company, Ltd.Inventors: Masakazu Sagou, Hideyo Fujii
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Patent number: 4678858Abstract: A process for producing ethanol which comprises reacting methanol, carbon monoxide and water in the presence of a catalyst comprising cobalt or a cobalt compound and a tertiary phosphine as an effective component is disclosed. A gaseous mixture obtained by burning heavy oil or coal having a relatively high content of carbon can be used as a raw material for producing ethanol.Type: GrantFiled: March 26, 1986Date of Patent: July 7, 1987Assignee: Agency of Industrial Science and TechnologyInventors: Nobuo Isogai, Takashi Okawa, Motoyuki Hosokawa, Tomoji Tsuji, Natsuko Wakui
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Patent number: 4628121Abstract: Acetaldehyde is prepared by reacting methanol with carbon monoxide and hydrogen in the presence of a catalyst comprising a cobalt component, a tin component, and a halogen component.Type: GrantFiled: September 27, 1985Date of Patent: December 9, 1986Assignee: The Halcon SD Group, Inc.Inventor: Nabil Rizkalla